Toluene → HCID 57786228, compound

HRID 1399346Notes

Reaction equation

HRID 1399346 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[N:16]([CH2:17][CH2:18][CH2:19][OH:20])[C:15]2[C:21]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:22][CH:23]=[CH:24][C:14]=2[N:13]=1)(O)[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH3:10])[C:12]2=[N:13][C:14]3[C:15](=[C:21]([N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])[CH:22]=[CH:23][CH:24]=3)[N:16]2[CH2:17][CH2:18][CH2:19][O:20]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68760893HCID 68760893, compound

Product 1

HCID 57786228HCID 57786228, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 3-{2-[1-(2,4-dichlorophenyl)-1-hydroxyethyl]-7-(diethylamino)-1H-benzimidazol-1-yl}propan-1-ol (Reference example 209, 210 mg, 0.500 mmol) and triphenylphosphine (157 mg, 0.600 mmol) in tetrahydrofuran (10 mL) was added a solution of diethyl azodicarboxylate in toluene (40%, 342 μL, 0.750 mmol) at room temperature. The mixture was stirred at 40° C. for 12 h, concentrated in vacuo, and purified by column chromatography on NH silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture to give a colorless amorphous (97.6 mg, 0.233 mmol, 47%).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography on NH silica gel eluting with a 5-20% ethyl acetate/n-hexane gradient mixture
  3. customto give a colorless amorphous (97.6 mg, 0.233 mmol, 47%)

Sources & evidence

ORD record
ord-7b10dc5830d94fac81001c33892f6f7d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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